AU649498B2 - Process for preparing 2R-methyl-4,4,4-trifluorobutylamine; process for preparing (R)-4-{5-N-{4,4,4-trifluoro-2- methylbutyl}carbamoyl)-1-methyl-indol-3-ylmethyl}-3- methoxy-N-tolylsulphonylbenzamide via said process and novel intermediates - Google Patents
Process for preparing 2R-methyl-4,4,4-trifluorobutylamine; process for preparing (R)-4-{5-N-{4,4,4-trifluoro-2- methylbutyl}carbamoyl)-1-methyl-indol-3-ylmethyl}-3- methoxy-N-tolylsulphonylbenzamide via said process and novel intermediatesInfo
- Publication number
- AU649498B2 AU649498B2 AU88385/91A AU8838591A AU649498B2 AU 649498 B2 AU649498 B2 AU 649498B2 AU 88385/91 A AU88385/91 A AU 88385/91A AU 8838591 A AU8838591 A AU 8838591A AU 649498 B2 AU649498 B2 AU 649498B2
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- preparing
- trifluorobutylamine
- methylbutyl
- trifluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 2
- 239000000543 intermediate Substances 0.000 title 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 abstract 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- ULMFXAMQUGLVGA-LJQANCHMSA-N 3-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-methyl-n-[(2r)-4,4,4-trifluoro-2-methylbutyl]indole-5-carboxamide Chemical compound C=1C=C(CC=2C3=CC(=CC=C3N(C)C=2)C(=O)NC[C@H](C)CC(F)(F)F)C(OC)=CC=1C(=O)NS(=O)(=O)C1=CC=CC=C1C ULMFXAMQUGLVGA-LJQANCHMSA-N 0.000 abstract 1
- OBUKEMPWKGDRJV-UHFFFAOYSA-N 4,4,4-trifluoro-2-methylbutanoic acid Chemical compound OC(=O)C(C)CC(F)(F)F OBUKEMPWKGDRJV-UHFFFAOYSA-N 0.000 abstract 1
- 206010039085 Rhinitis allergic Diseases 0.000 abstract 1
- 201000010105 allergic rhinitis Diseases 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/50—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of carboxylic acid amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/15—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Plant Substances (AREA)
- Carbon And Carbon Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909026425A GB9026425D0 (en) | 1990-12-05 | 1990-12-05 | Process |
| GB9026425 | 1990-12-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU8838591A AU8838591A (en) | 1992-06-11 |
| AU649498B2 true AU649498B2 (en) | 1994-05-26 |
Family
ID=10686507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU88385/91A Ceased AU649498B2 (en) | 1990-12-05 | 1991-12-04 | Process for preparing 2R-methyl-4,4,4-trifluorobutylamine; process for preparing (R)-4-{5-N-{4,4,4-trifluoro-2- methylbutyl}carbamoyl)-1-methyl-indol-3-ylmethyl}-3- methoxy-N-tolylsulphonylbenzamide via said process and novel intermediates |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5274118A (cs) |
| EP (1) | EP0489548B1 (cs) |
| JP (1) | JP3160041B2 (cs) |
| AT (1) | ATE115543T1 (cs) |
| AU (1) | AU649498B2 (cs) |
| CA (1) | CA2056068C (cs) |
| CZ (1) | CZ281659B6 (cs) |
| DE (1) | DE69105931T2 (cs) |
| DK (1) | DK0489548T3 (cs) |
| ES (1) | ES2066373T3 (cs) |
| FI (1) | FI109995B (cs) |
| GB (1) | GB9026425D0 (cs) |
| HU (1) | HU212936B (cs) |
| IE (1) | IE65663B1 (cs) |
| IL (1) | IL100092A (cs) |
| NO (1) | NO176516C (cs) |
| NZ (1) | NZ240857A (cs) |
| PT (1) | PT99684B (cs) |
| SK (1) | SK280473B6 (cs) |
| ZA (1) | ZA919572B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8927981D0 (en) * | 1989-12-11 | 1990-02-14 | Ici Plc | Carbamoyl derivative |
| GB9026427D0 (en) * | 1990-12-05 | 1991-01-23 | Ici Plc | Chemical process |
| GB9119001D0 (en) * | 1991-09-05 | 1991-10-23 | Ici Plc | Pharmaceutical agents |
| JPWO2005005648A1 (ja) * | 2003-07-11 | 2007-09-20 | 三菱ウェルファーマ株式会社 | 新規な光学活性カルボン酸の製造法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6791790A (en) * | 1989-12-11 | 1991-06-13 | Astrazeneca Ab | 5-(2-methyl-4,4,4-trifluorobutyl-carbamoyl)indole derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2243977A (en) * | 1938-07-18 | 1941-06-03 | Sandoz Ltd | Process for the preparation of amino-alcohols |
| US5105014A (en) * | 1991-08-06 | 1992-04-14 | Mallinckrodt Medical, Inc. | Synthesis of vicinal diamines |
-
1990
- 1990-12-05 GB GB909026425A patent/GB9026425D0/en active Pending
-
1991
- 1991-11-19 IL IL10009291A patent/IL100092A/en active IP Right Grant
- 1991-11-22 CA CA002056068A patent/CA2056068C/en not_active Expired - Fee Related
- 1991-11-29 DE DE69105931T patent/DE69105931T2/de not_active Expired - Fee Related
- 1991-11-29 EP EP91311073A patent/EP0489548B1/en not_active Expired - Lifetime
- 1991-11-29 DK DK91311073.0T patent/DK0489548T3/da active
- 1991-11-29 ES ES91311073T patent/ES2066373T3/es not_active Expired - Lifetime
- 1991-11-29 AT AT91311073T patent/ATE115543T1/de not_active IP Right Cessation
- 1991-12-02 HU HU913758A patent/HU212936B/hu not_active IP Right Cessation
- 1991-12-04 ZA ZA919572A patent/ZA919572B/xx unknown
- 1991-12-04 NZ NZ240857A patent/NZ240857A/xx not_active IP Right Cessation
- 1991-12-04 FI FI915721A patent/FI109995B/fi not_active IP Right Cessation
- 1991-12-04 CZ CS913687A patent/CZ281659B6/cs not_active IP Right Cessation
- 1991-12-04 IE IE421991A patent/IE65663B1/en not_active IP Right Cessation
- 1991-12-04 SK SK3687-91A patent/SK280473B6/sk unknown
- 1991-12-04 NO NO914776A patent/NO176516C/no unknown
- 1991-12-04 PT PT99684A patent/PT99684B/pt not_active IP Right Cessation
- 1991-12-04 US US07/803,291 patent/US5274118A/en not_active Expired - Fee Related
- 1991-12-04 AU AU88385/91A patent/AU649498B2/en not_active Ceased
- 1991-12-05 JP JP32180191A patent/JP3160041B2/ja not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6791790A (en) * | 1989-12-11 | 1991-06-13 | Astrazeneca Ab | 5-(2-methyl-4,4,4-trifluorobutyl-carbamoyl)indole derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| DK0489548T3 (da) | 1995-05-08 |
| NO914776D0 (no) | 1991-12-04 |
| AU8838591A (en) | 1992-06-11 |
| FI915721A7 (fi) | 1992-06-06 |
| IL100092A0 (en) | 1992-08-18 |
| IL100092A (en) | 1996-10-16 |
| PT99684B (pt) | 1999-05-31 |
| US5274118A (en) | 1993-12-28 |
| CS368791A3 (en) | 1992-09-16 |
| DE69105931D1 (de) | 1995-01-26 |
| CA2056068C (en) | 2003-05-06 |
| EP0489548A1 (en) | 1992-06-10 |
| FI915721A0 (fi) | 1991-12-04 |
| SK280473B6 (sk) | 2000-02-14 |
| ATE115543T1 (de) | 1994-12-15 |
| JPH04290870A (ja) | 1992-10-15 |
| HU212936B (en) | 1996-12-30 |
| IE65663B1 (en) | 1995-11-15 |
| NZ240857A (en) | 1994-05-26 |
| HUT61964A (en) | 1993-03-29 |
| PT99684A (pt) | 1992-10-30 |
| CZ281659B6 (cs) | 1996-12-11 |
| CA2056068A1 (en) | 1992-06-06 |
| FI109995B (fi) | 2002-11-15 |
| GB9026425D0 (en) | 1991-01-23 |
| NO176516B (no) | 1995-01-09 |
| JP3160041B2 (ja) | 2001-04-23 |
| NO176516C (no) | 1995-04-19 |
| DE69105931T2 (de) | 1995-05-04 |
| IE914219A1 (en) | 1992-06-17 |
| ZA919572B (en) | 1992-10-28 |
| ES2066373T3 (es) | 1995-03-01 |
| NO914776L (no) | 1992-06-09 |
| HU913758D0 (en) | 1992-02-28 |
| EP0489548B1 (en) | 1994-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Assignment registered |
Owner name: ASTRAZENECA AB Free format text: FORMER OWNER WAS: ZENECA LIMITED |